EP2271677A1 - Strukturviskose peroxiddispersionen - Google Patents

Strukturviskose peroxiddispersionen

Info

Publication number: EP2271677A1
Authority: EP; European Patent Office
Prior art keywords: sodium; aqueous dispersion; peroxide; group; lauroyl
Prior art date: 2008-05-01
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

EP09739752A

Other languages

English (en)

French (fr)

Other versions

EP2271677A4 (de

Inventor

Thomas H. Kozel

Joseph M. Gravelle

Sri R. Seshadri

Tomas Salvador

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Arkema Inc

Original Assignee

Arkema Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2008-05-01

Filing date

2009-04-30

Publication date

2011-01-12

2009-04-30 Application filed by Arkema Inc filed Critical Arkema Inc

2011-01-12 Publication of EP2271677A1 publication Critical patent/EP2271677A1/de

2011-09-21 Publication of EP2271677A4 publication Critical patent/EP2271677A4/de

Status Withdrawn legal-status Critical Current

Links

239000006185 dispersion Substances 0.000 title claims abstract description 44
150000002978 peroxides Chemical class 0.000 title abstract description 14
150000001451 organic peroxides Chemical class 0.000 claims abstract description 19
239000004094 surface-active agent Substances 0.000 claims abstract description 11
-1 ketone peroxides Chemical class 0.000 claims description 52
239000000203 mixture Substances 0.000 claims description 18
239000003945 anionic surfactant Substances 0.000 claims description 10
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 9
229910052708 sodium Inorganic materials 0.000 claims description 9
239000011734 sodium Substances 0.000 claims description 9
229940104261 taurate Drugs 0.000 claims description 9
229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 7
239000004342 Benzoyl peroxide Substances 0.000 claims description 7
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 7
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 7
235000019400 benzoyl peroxide Nutrition 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 7
229910052700 potassium Inorganic materials 0.000 claims description 7
239000011591 potassium Substances 0.000 claims description 7
XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 claims description 7
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 claims description 6
AOHBGMDQHXJADT-UHFFFAOYSA-N 2-(2-dodecanoyloxypropanoyloxy)propanoic acid Chemical compound CCCCCCCCCCCC(=O)OC(C)C(=O)OC(C)C(O)=O AOHBGMDQHXJADT-UHFFFAOYSA-N 0.000 claims description 6
239000012933 diacyl peroxide Substances 0.000 claims description 6
229920001451 polypropylene glycol Polymers 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 5
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims description 5
235000014113 dietary fatty acids Nutrition 0.000 claims description 5
239000000194 fatty acid Substances 0.000 claims description 5
229930195729 fatty acid Natural products 0.000 claims description 5
150000002306 glutamic acid derivatives Chemical class 0.000 claims description 5
235000019333 sodium laurylsulphate Nutrition 0.000 claims description 5
ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 claims description 4
108010077895 Sarcosine Proteins 0.000 claims description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
150000001768 cations Chemical class 0.000 claims description 4
108700004121 sarkosyl Proteins 0.000 claims description 4
KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 claims description 4
229940045885 sodium lauroyl sarcosinate Drugs 0.000 claims description 4
229940060304 sodium myristoyl sarcosinate Drugs 0.000 claims description 4
ZUFONQSOSYEWCN-UHFFFAOYSA-M sodium;2-(methylamino)acetate Chemical compound [Na+].CNCC([O-])=O ZUFONQSOSYEWCN-UHFFFAOYSA-M 0.000 claims description 4
KHCOJQDJOCNUGV-UHFFFAOYSA-M sodium;2-[methyl(tetradecanoyl)amino]acetate Chemical compound [Na+].CCCCCCCCCCCCCC(=O)N(C)CC([O-])=O KHCOJQDJOCNUGV-UHFFFAOYSA-M 0.000 claims description 4
229910019142 PO4 Inorganic materials 0.000 claims description 3
125000001931 aliphatic group Chemical group 0.000 claims description 3
125000005910 alkyl carbonate group Chemical group 0.000 claims description 3
BTBJBAZGXNKLQC-UHFFFAOYSA-N ammonium lauryl sulfate Chemical compound [NH4+].CCCCCCCCCCCCOS([O-])(=O)=O BTBJBAZGXNKLQC-UHFFFAOYSA-N 0.000 claims description 3
229940063953 ammonium lauryl sulfate Drugs 0.000 claims description 3
239000002280 amphoteric surfactant Substances 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
235000021317 phosphate Nutrition 0.000 claims description 3
150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 3
229920006395 saturated elastomer Polymers 0.000 claims description 3
WRXCBRHBHGNNQA-UHFFFAOYSA-N (2,4-dichlorobenzoyl) 2,4-dichlorobenzenecarboperoxoate Chemical compound ClC1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1Cl WRXCBRHBHGNNQA-UHFFFAOYSA-N 0.000 claims description 2
JMYZLRSSLFFUQN-UHFFFAOYSA-N (2-chlorobenzoyl) 2-chlorobenzenecarboperoxoate Chemical compound ClC1=CC=CC=C1C(=O)OOC(=O)C1=CC=CC=C1Cl JMYZLRSSLFFUQN-UHFFFAOYSA-N 0.000 claims description 2
WOTCBNVQQFUGLX-UHFFFAOYSA-N (2-methoxybenzoyl) 2-methoxybenzenecarboperoxoate Chemical compound COC1=CC=CC=C1C(=O)OOC(=O)C1=CC=CC=C1OC WOTCBNVQQFUGLX-UHFFFAOYSA-N 0.000 claims description 2
ZICNIEOYWVIEQJ-UHFFFAOYSA-N (2-methylbenzoyl) 2-methylbenzenecarboperoxoate Chemical compound CC1=CC=CC=C1C(=O)OOC(=O)C1=CC=CC=C1C ZICNIEOYWVIEQJ-UHFFFAOYSA-N 0.000 claims description 2
JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 claims description 2
NOBYOEQUFMGXBP-UHFFFAOYSA-N (4-tert-butylcyclohexyl) (4-tert-butylcyclohexyl)oxycarbonyloxy carbonate Chemical compound C1CC(C(C)(C)C)CCC1OC(=O)OOC(=O)OC1CCC(C(C)(C)C)CC1 NOBYOEQUFMGXBP-UHFFFAOYSA-N 0.000 claims description 2
KZRXPHCVIMWWDS-AWEZNQCLSA-N (4S)-4-amino-5-dodecanoyloxy-5-oxopentanoic acid Chemical compound CCCCCCCCCCCC(=O)OC(=O)[C@@H](N)CCC(O)=O KZRXPHCVIMWWDS-AWEZNQCLSA-N 0.000 claims description 2
FDCJDKXCCYFOCV-UHFFFAOYSA-N 1-hexadecoxyhexadecane Chemical compound CCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCC FDCJDKXCCYFOCV-UHFFFAOYSA-N 0.000 claims description 2
DGSNTUCORHZCPV-UHFFFAOYSA-N 1-hydroperoxy-1-(1-hydroperoxycyclohexyl)peroxycyclohexane Chemical compound C1CCCCC1(OO)OOC1(OO)CCCCC1 DGSNTUCORHZCPV-UHFFFAOYSA-N 0.000 claims description 2
POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 2
CTXGTHVAWRBISV-UHFFFAOYSA-N 2-hydroxyethyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCCO CTXGTHVAWRBISV-UHFFFAOYSA-N 0.000 claims description 2
RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 claims description 2
XVTDINVUVOXJIY-UHFFFAOYSA-N 2-hydroxypropanoyl hexanoate Chemical compound CCCCCC(=O)OC(=O)C(C)O XVTDINVUVOXJIY-UHFFFAOYSA-N 0.000 claims description 2
VCNPGCHIKPSUSP-UHFFFAOYSA-N 2-hydroxypropyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OCC(C)O VCNPGCHIKPSUSP-UHFFFAOYSA-N 0.000 claims description 2
MZPBGKHCHOCSOL-UHFFFAOYSA-N 3-(dodecylamino)propanoic acid;sodium Chemical compound [Na].CCCCCCCCCCCCNCCC(O)=O MZPBGKHCHOCSOL-UHFFFAOYSA-N 0.000 claims description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 2
YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 claims description 2
NWGKJDSIEKMTRX-AAZCQSIUSA-N Sorbitan monooleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-AAZCQSIUSA-N 0.000 claims description 2
IYFATESGLOUGBX-YVNJGZBMSA-N Sorbitan monopalmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O IYFATESGLOUGBX-YVNJGZBMSA-N 0.000 claims description 2
HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 claims description 2
229930006000 Sucrose Natural products 0.000 claims description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 2
LWZFANDGMFTDAV-BURFUSLBSA-N [(2r)-2-[(2r,3r,4s)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl] dodecanoate Chemical group CCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O LWZFANDGMFTDAV-BURFUSLBSA-N 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
150000001408 amides Chemical class 0.000 claims description 2
229940098323 ammonium cocoyl isethionate Drugs 0.000 claims description 2
OCSIXPGPUXCISD-UHFFFAOYSA-N azane;2-[dodecanoyl(methyl)amino]acetic acid Chemical compound N.CCCCCCCCCCCC(=O)N(C)CC(O)=O OCSIXPGPUXCISD-UHFFFAOYSA-N 0.000 claims description 2
OADXQALOSREDRB-UHFFFAOYSA-N azanium;hexadecyl sulfate Chemical compound N.CCCCCCCCCCCCCCCCOS(O)(=O)=O OADXQALOSREDRB-UHFFFAOYSA-N 0.000 claims description 2
229920001400 block copolymer Polymers 0.000 claims description 2
125000001589 carboacyl group Chemical group 0.000 claims description 2
239000004359 castor oil Substances 0.000 claims description 2
235000019438 castor oil Nutrition 0.000 claims description 2
239000007795 chemical reaction product Substances 0.000 claims description 2
229940071124 cocoyl glutamate Drugs 0.000 claims description 2
XJOBOFWTZOKMOH-UHFFFAOYSA-N decanoyl decaneperoxoate Chemical compound CCCCCCCCCC(=O)OOC(=O)CCCCCCCCC XJOBOFWTZOKMOH-UHFFFAOYSA-N 0.000 claims description 2
SMVRDGHCVNAOIN-UHFFFAOYSA-L disodium;1-dodecoxydodecane;sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O.CCCCCCCCCCCCOCCCCCCCCCCCC SMVRDGHCVNAOIN-UHFFFAOYSA-L 0.000 claims description 2
KSDGSKVLUHKDAL-UHFFFAOYSA-L disodium;3-[2-carboxylatoethyl(dodecyl)amino]propanoate Chemical compound [Na+].[Na+].CCCCCCCCCCCCN(CCC([O-])=O)CCC([O-])=O KSDGSKVLUHKDAL-UHFFFAOYSA-L 0.000 claims description 2
POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 claims description 2
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 2
229940075507 glyceryl monostearate Drugs 0.000 claims description 2
229940075529 glyceryl stearate Drugs 0.000 claims description 2
QWVBGCWRHHXMRM-UHFFFAOYSA-N hexadecoxycarbonyloxy hexadecyl carbonate Chemical compound CCCCCCCCCCCCCCCCOC(=O)OOC(=O)OCCCCCCCCCCCCCCCC QWVBGCWRHHXMRM-UHFFFAOYSA-N 0.000 claims description 2
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical class OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 claims description 2
229940070765 laurate Drugs 0.000 claims description 2
229940071085 lauroyl glutamate Drugs 0.000 claims description 2
229940094506 lauryl betaine Drugs 0.000 claims description 2
IZWSFJTYBVKZNK-UHFFFAOYSA-N lauryl sulfobetaine Chemical compound CCCCCCCCCCCC[N+](C)(C)CCCS([O-])(=O)=O IZWSFJTYBVKZNK-UHFFFAOYSA-N 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
239000001788 mono and diglycerides of fatty acids Substances 0.000 claims description 2
LPUQAYUQRXPFSQ-DFWYDOINSA-M monosodium L-glutamate Chemical compound [Na+].[O-]C(=O)[C@@H](N)CCC(O)=O LPUQAYUQRXPFSQ-DFWYDOINSA-M 0.000 claims description 2
229940070800 myristoyl glutamate Drugs 0.000 claims description 2
125000001419 myristoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
QCTVGFNUKWXQNN-UHFFFAOYSA-N n-(2-hydroxypropyl)octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCC(C)O QCTVGFNUKWXQNN-UHFFFAOYSA-N 0.000 claims description 2
BOUCRWJEKAGKKG-UHFFFAOYSA-N n-[3-(diethylaminomethyl)-4-hydroxyphenyl]acetamide Chemical compound CCN(CC)CC1=CC(NC(C)=O)=CC=C1O BOUCRWJEKAGKKG-UHFFFAOYSA-N 0.000 claims description 2
DVEKCXOJTLDBFE-UHFFFAOYSA-N n-dodecyl-n,n-dimethylglycinate Chemical compound CCCCCCCCCCCC[N+](C)(C)CC([O-])=O DVEKCXOJTLDBFE-UHFFFAOYSA-N 0.000 claims description 2
239000002736 nonionic surfactant Substances 0.000 claims description 2
229920002114 octoxynol-9 Polymers 0.000 claims description 2
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
125000005634 peroxydicarbonate group Chemical group 0.000 claims description 2
229920002523 polyethylene Glycol 1000 Polymers 0.000 claims description 2
229940056099 polyglyceryl-4 oleate Drugs 0.000 claims description 2
229920000136 polysorbate Polymers 0.000 claims description 2
229940068965 polysorbates Drugs 0.000 claims description 2
229940080236 sodium cetyl sulfate Drugs 0.000 claims description 2
229940079781 sodium cocoyl glutamate Drugs 0.000 claims description 2
229940057950 sodium laureth sulfate Drugs 0.000 claims description 2
229940045944 sodium lauroyl glutamate Drugs 0.000 claims description 2
229940048106 sodium lauroyl isethionate Drugs 0.000 claims description 2
229940077092 sodium myristoyl glutamate Drugs 0.000 claims description 2
229940102541 sodium trideceth sulfate Drugs 0.000 claims description 2
IWIUXJGIDSGWDN-UQKRIMTDSA-M sodium;(2s)-2-(dodecanoylamino)pentanedioate;hydron Chemical compound [Na+].CCCCCCCCCCCC(=O)N[C@H](C([O-])=O)CCC(O)=O IWIUXJGIDSGWDN-UQKRIMTDSA-M 0.000 claims description 2
FCBUGCHAVCFTHW-NTISSMGPSA-N sodium;(2s)-2-(tetradecanoylamino)pentanedioic acid Chemical compound [Na].CCCCCCCCCCCCCC(=O)N[C@H](C(O)=O)CCC(O)=O FCBUGCHAVCFTHW-NTISSMGPSA-N 0.000 claims description 2
NTYZDAJPNNBYED-UHFFFAOYSA-M sodium;2-(2-dodecanoyloxypropanoyloxy)propanoate Chemical compound [Na+].CCCCCCCCCCCC(=O)OC(C)C(=O)OC(C)C([O-])=O NTYZDAJPNNBYED-UHFFFAOYSA-M 0.000 claims description 2
AMJZVHHOVFFTOM-UHFFFAOYSA-M sodium;2-(2-hexanoyloxypropanoyloxy)propanoate Chemical compound [Na+].CCCCCC(=O)OC(C)C(=O)OC(C)C([O-])=O AMJZVHHOVFFTOM-UHFFFAOYSA-M 0.000 claims description 2
SXHLENDCVBIJFO-UHFFFAOYSA-M sodium;2-[2-(2-dodecoxyethoxy)ethoxy]ethyl sulfate Chemical compound [Na+].CCCCCCCCCCCCOCCOCCOCCOS([O-])(=O)=O SXHLENDCVBIJFO-UHFFFAOYSA-M 0.000 claims description 2
KLYDBHUQNXKACI-UHFFFAOYSA-M sodium;2-[2-(2-tridecoxyethoxy)ethoxy]ethyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCOCCOCCOCCOS([O-])(=O)=O KLYDBHUQNXKACI-UHFFFAOYSA-M 0.000 claims description 2
IDXHDUOOTUFFOX-UHFFFAOYSA-M sodium;2-[2-hydroxyethyl-[2-(tetradecanoylamino)ethyl]amino]acetate Chemical compound [Na+].CCCCCCCCCCCCCC(=O)NCCN(CCO)CC([O-])=O IDXHDUOOTUFFOX-UHFFFAOYSA-M 0.000 claims description 2
CAVXVRQDZKMZDB-UHFFFAOYSA-M sodium;2-[dodecanoyl(methyl)amino]ethanesulfonate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CCS([O-])(=O)=O CAVXVRQDZKMZDB-UHFFFAOYSA-M 0.000 claims description 2
BRMSVEGRHOZCAM-UHFFFAOYSA-M sodium;2-dodecanoyloxyethanesulfonate Chemical compound [Na+].CCCCCCCCCCCC(=O)OCCS([O-])(=O)=O BRMSVEGRHOZCAM-UHFFFAOYSA-M 0.000 claims description 2
GGHPAKFFUZUEKL-UHFFFAOYSA-M sodium;hexadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O GGHPAKFFUZUEKL-UHFFFAOYSA-M 0.000 claims description 2
229940100515 sorbitan Drugs 0.000 claims description 2
229950006451 sorbitan laurate Drugs 0.000 claims description 2
235000011067 sorbitan monolaureate Nutrition 0.000 claims description 2
229950004959 sorbitan oleate Drugs 0.000 claims description 2
229950003429 sorbitan palmitate Drugs 0.000 claims description 2
229950011392 sorbitan stearate Drugs 0.000 claims description 2
JDVPQXZIJDEHAN-UHFFFAOYSA-N succinamic acid Chemical class NC(=O)CCC(O)=O JDVPQXZIJDEHAN-UHFFFAOYSA-N 0.000 claims description 2
239000005720 sucrose Substances 0.000 claims description 2
150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 2
239000003760 tallow Substances 0.000 claims description 2
SLFUZVJZPBHLAQ-UHFFFAOYSA-N tetradecanoyl tetradecaneperoxoate Chemical compound CCCCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCCCC SLFUZVJZPBHLAQ-UHFFFAOYSA-N 0.000 claims description 2
239000008180 pharmaceutical surfactant Substances 0.000 claims 2
229940071089 sarcosinate Drugs 0.000 claims 2
BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 claims 1
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 1
229930195712 glutamate Natural products 0.000 claims 1
239000002270 dispersing agent Substances 0.000 abstract description 15
125000000129 anionic group Chemical group 0.000 abstract description 8
239000007787 solid Substances 0.000 abstract description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 7
239000003995 emulsifying agent Substances 0.000 abstract description 5
230000015572 biosynthetic process Effects 0.000 abstract description 2
239000002562 thickening agent Substances 0.000 abstract description 2
239000000839 emulsion Substances 0.000 description 4
239000000463 material Substances 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
229920001213 Polysorbate 20 Polymers 0.000 description 3
239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 3
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 2
239000007900 aqueous suspension Substances 0.000 description 2
230000004071 biological effect Effects 0.000 description 2
229940068977 polysorbate 20 Drugs 0.000 description 2
239000002904 solvent Substances 0.000 description 2
229960003080 taurine Drugs 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
229910006067 SO3−M Inorganic materials 0.000 description 1
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
239000000084 colloidal system Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
230000005611 electricity Effects 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
239000002360 explosive Substances 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000003999 initiator Substances 0.000 description 1
230000007794 irritation Effects 0.000 description 1
238000000034 method Methods 0.000 description 1
229920001983 poloxamer Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
230000035939 shock Effects 0.000 description 1
229940045998 sodium isethionate Drugs 0.000 description 1
LADXKQRVAFSPTR-UHFFFAOYSA-M sodium;2-hydroxyethanesulfonate Chemical compound [Na+].OCCS([O-])(=O)=O LADXKQRVAFSPTR-UHFFFAOYSA-M 0.000 description 1
239000000243 solution Substances 0.000 description 1
230000003068 static effect Effects 0.000 description 1
239000002352 surface water Substances 0.000 description 1
238000010557 suspension polymerization reaction Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/28—Oxygen or compounds releasing free oxygen
- C08F4/32—Organic compounds
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/14—Peroxides

Definitions

the present invention relates to pharmaceutically acceptable aqueous dispersions of normally solid organic peroxides.
the dispersions are pastes which contain high concentrations of the peroxide.
the pastes are shear thinning so as to be pumpable/pourable when mixed or stirred which makes their handling and use easier.
Peroxides have, as a general property, a tendency to be flammable and explosive with some peroxides exhibiting such properties to a greater extent than others.
benzoyl peroxide may decompose when dry due to shock, friction, or static electricity.
This property carries with it the obvious hazards to the users of these materials as well as to the manufacturers and intermediate handlers thereof.
One particularly burdensome aspect of this property occurs during shipment of the peroxides. Accordingly, it has long been an object to provide flame resistant organic peroxide compositions.
U.S. Pat. No. 3,507,800 is directed to providing a flame resistant peroxide composition consisting essentially of three components- water, peroxide and solvent wherein the water is at least about 18 percent of the composition.
U.S. Pat. No. 3,825,509 describes a process for the suspension polymerization of vinyl chloride wherein the initiator is an aqueous emulsion of an organic peroxide in which the peroxide is present in an amount up to 19 weight percent.
the surfactant used to prepare the aqueous peroxide emulsion is a combination of polyvinyl alcohol and polyoxyethylene sorbitan monolaurate.
emulsions containing greater than about 19 percent by weight of organic peroxide are described as being too viscous and therefore difficult to handle.
U.S. Pat. Nos. 4,039,475 and 4,092,470 disclose stable, pumpable aqueous suspensions of organic peroxides using a mixture of a) nonionic emulsifiers having a maximum HLB value of 12.5 and b) nonionic emulsifiers having a minimum HLB value of 12.5 or anionic emulsifiers.
U.S. Pat. No. 4,734,135 discloses aqueous suspensions of solid organic peroxides using a protective colloid, a surface active agent and water.
U.S. Pat. No. 4,440,885 teaches emulsions of a solid organic peroxide using an emulsif ⁇ er having an HLB value from about 9 to about 20, a hydrocarbon solvent and water.
the present aqueous dispersions comprise more than about 40 percent by weight of an organic peroxide which is normally solid, an effective dispersing amount of a pharmaceutically acceptable dispersing agent and water. It was discovered that the addition of a dispersing agent/surfactant to a non-flowing organic paste resulted in the formation of a shear thinning aqueous dispersion.
the aqueous dispersions can also contain optional components such as thickening agents and anionic emulsifiers.
Aqueous dispersions of the present invention comprise an organic peroxide which is normally solid and a pharmaceutically acceptable dispersing agent/surfactant.
organic peroxides are aromatic diacyl peroxides, such as benzoyl peroxide, o-methylbenzoyl peroxide, o-methoxybenzoyl peroxide, o-ethoxy benzoyl peroxide, o-chlorobenzoyl peroxide and 2, 4-dichlorobenzoyl peroxide; aliphatic diacyl peroxides, such as decanoyl peroxide, lauroyl peroxide and myristoyl peroxide; ketone peroxides, such as 1 -hydroxy cyclohexyl peroxide and 1- hydroperoxycyclohexyl peroxide; aldehyde peroxides such as 1 -hydroxy heptyl peroxide; peroxy dicarbonates such as dicetyl peroxydicarbonate, di(4-t- butylcyclohexyl) peroxydicarbonate and acylperoxy alkylcarbonates, such as ace
the present aqueous dispersions comprise about 40 percent or more by weight of an organic peroxide.
One of the features of the present invention is that it enables the preparation of aqueous dispersions containing about 40 or more percent by weight of organic peroxide which dispersions are pumpable because they are shear thinning.
shear thinning means that viscosity drops as the shear rate increases.
the viscosity of the peroxide dispersions of the present invention will drop as the dispersion is stirred or mixed and it becomes pourable or pumpable easing use.
a pharmaceutically acceptable dispersing agent refers to a dispersing agent that does not cause significant irritation to an organism and does not abrogate the biological activity and properties of an administered compound that the dispersion of the present invention is combined with.
composition of the present invention al'so comprise one or more pharmaceutically acceptable dispersing agents or surfactants in an amount of from about 0.5 to 2.0 wt%.
pharmaceutically acceptable dispersing agents include those selected from the group consisting of anionic surfactants, nonionic surfactants, amphoteric surfactants, and mixtures thereof.
Nonlimiting examples of nonionic pharmaceutically acceptable dispersing agents or surfactants useful in the composition of the present invention include those selected from the group consisting of sodium lauryl ether sulfate, sodium lauryl sulfate, ethylene glycol monostearate, propylene glycol myristate, glyceryl monostearate, glyceryl stearate, polyglyceryl-4-oleate, sorbitan acylate, sucrose acylate, PEG- 150 laurate, PEG-400 monolaurate, polyoxyethylene monolaurate, polysorbates, polyoxyethylene octylphenylether, PEG-1000 cetyl ether, polyoxyethylene tridecyl ether, polypropylene glycol butyl ether, Polyethlylene-polypropylene glycol, stearoyl monoisopropanolamide, polyoxyethylene hydrogenated tallow amide, polyoxyethylene fatty acid esters (T weens), the block copo
Nonlimiting examples of amphoteric pharmaceutically acceptable dispersing agents or surfactants useful in the composition of the present invention include those selected from the group consisting of sodium N-dodecyl-beta-alanin-e, sodium N-lauryl-beta- iminodipropionate, myristoamphoacetate, lauryl betaine and lauryl sulfobetaine.
anionic pharmaceutically acceptable dispersing agents or surfactants useful in the compositions of the present invention include those selected from the group consisting of sarcosinates, sulfates, isethionates, taurates, phosphates, lactylates, glutamates, and mixtures thereof.
Another suitable class of anionic surfactants are the water-soluble salts of the organic, sulfuric acid reaction products of the general formula: Rl-SO 3 -M wherein Rl is chosen from the group consisting of a straight or branched chain, saturated aliphatic hydrocarbon radical having from about 8 to about 24, preferably about 10 to about 16, carbon atoms; and M is a cation.
anionic synthetic surfactants include the class designated as succinamates, olefin sulfonates having about 12 to about 24 carbon atoms, and b-alkyloxy alkane sulfonates. Examples of these materials are sodium lauryl sulfate and ammonium lauryl sulfate.
anionic materials include phosphates such as monoalkyl, dialkyl, and trialkylphosphate salts.
alkanoyl sarcosinates corresponding to the formula RCON(CH 3 )CH 2 CH 2 CO 2 M wherein R is alkyl or alkenyl of about 10 to about 20 carbon atoms, and M is a water-soluble cation such as ammonium, sodium, potassium and alkanolamine (e.g., triethanolamine), a preferred examples of which are sodium lauroyl sarcosinate, sodium cocoyl sarcosinate, ammonium lauroyl sarcosinate, and sodium myristoyl sarcosinate.
TEA salts of sarcosinates are also useful.
taurates which are based on taurine, which is also known as 2-aminoethanesulfonic acid. Especially useful are taurates having carbon chains between C 8 and C 16 .
taurates include N-alkyltaurines such as the one prepared by reacting dodecylarmne with sodium isethionate according to the teaching of U.S. Pat No. 2,658,072 which is incorporated herein by reference in its entirety.
Further nonlimiting examples include ammonium, sodium, potassium and alkanolamine (e.g., triethanolamine) salts of lauroyl methyl taurate, myristoyl methyl taurate, and cocoyl methyl taurate.
lactylates especially those having carbon chains between C 8 and C 16 .
lactylates include ammonium, sodium, potassium and alkanolamine (e.g., triethanolamine) salts of lauroyl lactylate, cocoyl lactylate, lauroyl lactylate, and caproyl lactylate.
anionic surfactants comprising glutamates, especially those having carbon chains between C 8 and Ci 6 .
glutamates include ammonium, sodium, potassium and alkanolamine (e.g., triethanolamine) salts of lauroyl glutamate, myristoyl glutamate, and cocoyl glutamate. . ' . - ⁇ ⁇ ⁇
Nonlimiting examples of preferred anionic surfactants useful herein include those selected from the group consisting of sodium lauryl sulfate, ammonium lauryl sulfate, ammonium laureth sulfate, sodium laureth sulfate, sodium trideceth sulfate, ammonium cetyl sulfate, sodium cetyl sulfate, ammonium cocoyl isethionate, sodium lauroyl isethionate, sodium lauroyl lactylate, triethanolamine lauroyl lactylate, sodium caproyl lactylate, sodium lauroyl sarcosinate, sodium myristoyl sarcosinate, sodium cocoyl sarcosinate, sodium lauroyl methyl taurate, sodium cocoyl methyl taurate, sodium lauroyl glutamate, sodium myristoyl glutamate, and sodium cocoyl glutamate and mixtures thereof.
aqueous solution of 50% by weight benzoyl peroxide and 0.25% by weight polysorbate 20 was prepared and allowed to stand for two weeks. Viscosity was measure with a Brookfield viscometer, using an RV-3 spindle at lOrpm at 2O 0 C. The viscosity after standing was about 8,5000-10,000 centipoise. After vigorous shaking the viscosity dropped to about 2,450-3,100 centipose.
Aqueous solutions of 50% by weight benzoyl peroxide were prepared having 0, 0.25, 0.50 and 1.00% by weight polysorbate 20.
the viscosity of each solution was measured with a Brookf ⁇ eld viscometer using a TC spindle at 1.5rpm at 2O 0 C, helipath. The viscosities are summarized in Table 1.

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Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Medicinal Preparation (AREA)
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EP09739752A 2008-05-01 2009-04-30 Strukturviskose peroxiddispersionen Withdrawn EP2271677A4 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US4951808P	2008-05-01	2008-05-01
PCT/US2009/042201 WO2009134950A1 (en)	2008-05-01	2009-04-30	Shear thinning peroxide dispersions

Publications (2)

Publication Number	Publication Date
EP2271677A1 true EP2271677A1 (de)	2011-01-12
EP2271677A4 EP2271677A4 (de)	2011-09-21

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EP09739752A Withdrawn EP2271677A4 (de)	2008-05-01	2009-04-30	Strukturviskose peroxiddispersionen

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US (1)	US20110086959A1 (de)
EP (1)	EP2271677A4 (de)
CN (1)	CN102015778A (de)
WO (1)	WO2009134950A1 (de)

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Publication number	Priority date	Publication date	Assignee	Title
US9217044B2 (en)	2009-02-03	2015-12-22	Arkema Inc.	Thixotropic anhydrous shear thinning peroxide dispersions
US9861119B2 (en)	2012-06-15	2018-01-09	Arkema Inc.	Peroxide dispersions
EP2861688B1 (de) *	2012-06-15	2019-04-24	Arkema, Inc.	Peroxiddispersionen
US11560535B2 (en)	2016-06-09	2023-01-24	Arkema Inc.	Organic peroxide dispersions

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2009
- 2009-04-30 EP EP09739752A patent/EP2271677A4/de not_active Withdrawn
- 2009-04-30 US US12/989,828 patent/US20110086959A1/en not_active Abandoned
- 2009-04-30 CN CN2009801165564A patent/CN102015778A/zh active Pending
- 2009-04-30 WO PCT/US2009/042201 patent/WO2009134950A1/en not_active Ceased

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WO2009134950A1 (en)	2009-11-05
US20110086959A1 (en)	2011-04-14
CN102015778A (zh)	2011-04-13

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